Compound, resin precursor, cured object, optical element, optical system, interchangeable camera lens, optical device, cemented lens, and method for manufacturing cemented lens

ABSTRACT

A compound represented by Formula (1) given below. (In the formula, R1 represents a hydrogen atom or a methyl group, X1 represents a C1 to 9 alkylene group, or a C3 to 6 alkylene group in which at least one hydrogen is replaced with an acryloxy group or a methacryloxy group, l1 represents an integer from 0 to 3, Q1 represents a hydrogen atom or Formula (2) given below (In the formula, R2 represents a hydrogen atom or a methyl group, X2 represents a C1 to 9 alkylene group, or a C3 to 6 alkylene group in which at least one hydrogen is replaced with an acryloxy group or a methacryloxy group, l2 represents an integer from 0 to 3, and * represents a bonding site), and Q2 represents a hydrogen atom or Formula (3) given below (In the formula, R3 represents a hydrogen atom or a methyl group, X3 represents a C1 to 9 alkylene group, or a C3 to 6 alkylene group in which at least one hydrogen is replaced with an acryloxy group or a methacryloxy group, l3 represents an integer from 0 to 3, and * represents a bonding site).)

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation application, filed under 35 U.S.C. §111(a), of International Application PCT/JP2020/018439, filed May 1,2020, the contents of which are incorporated herein by reference.

TECHNICAL FIELD

The present invention relates to a compound, a resin precursor, a curedobject, an optical element, an optical system, an interchangeable cameralens, an optical device, a cemented lens, and a method for manufacturingcemented lens.

BACKGROUND ART

For example, JP 2016-095542 A (PTL 1) discloses a cemented lens obtainedby adhering an object-side lens having negative power and an image-sidelens having positive power by using a resin adhesive layer. Forsatisfactory correction of chromatic aberrations, a material having alarge θ_(g,F) value is demanded for the resin adhesive layer used insuch cemented lens.

PTL 1: JP 2016-095542 A

SUMMARY

A first aspect according to the present invention is a compoundrepresented by Formula (1) given below.

(In the formula, R₁ represents a hydrogen atom or a methyl group,X¹ represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an acryloxy groupor a methacryloxy group, l¹ represents an integer from 0 to 3, Q¹represents a hydrogen atom or Formula (2) given below

(In the formula, R² represents a hydrogen atom or a methyl group,X² represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an acryloxy groupor a methacryloxy group, l² represents an integer from 0 to 3, and *represents a bonding site), andQ² represents a hydrogen atom or Formula (3) given below

(In the formula, R³ represents a hydrogen atom or a methyl group,X³ represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an acryloxy groupor a methacryloxy group, l³ represents an integer from 0 to 3, and *represents a bonding site).)

A second aspect according to the present invention is a resin precursorcontaining the compound described above and a curable composition.

A third aspect according to the present invention is a cured objectobtained by curing the resin precursor described above.

A fourth aspect according to the present invention is an optical elementusing the cured object described above.

A fifth aspect according to the present invention is an optical systemincluding the optical element described above.

A sixth aspect according to the present invention is an interchangeablecamera lens including the optical system described above.

A seventh aspect according to the present invention is an optical deviceincluding the optical system described above.

An eighth aspect according to the present invention is a cemented lensincluding a first lens element and a second lens element joined witheach other through intermediation of the cured object described above.

A ninth aspect according to the present invention is a method ofmanufacturing a cemented lens including a contacting step of contactinga first lens element and a second lens element with each other throughintermediation of the resin precursor described above, and a joiningstep of curing the resin precursor described above to join the firstlens element and the second lens element with each other.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a perspective view of one example of an optical deviceaccording to the present embodiment as an imaging device;

FIG. 2 is a front view of another example of the optical deviceaccording to the present embodiment as an imaging device;

FIG. 3 is a back view of the imaging device of FIG. 2 ;

FIG. 4 is a block diagram illustrating one example of the optical deviceaccording to the present embodiment as a multi-photon microscope;

FIG. 5 is a schematic view illustrating one example of a cemented lensaccording to the present embodiment; and

FIG. 6 is a graph illustrating results of an inner transmittance inexamples.

DETAILED DESCRIPTION

An embodiment of the present invention (hereinafter, simply referred toas the “present embodiment”) is described in detail. The presentembodiment described below is an example for describing the presentinvention, and is not intended to limit the present invention to thecontents described below. Note that, in the drawings, a positionalrelationship such as up, down, right, left, and the like is based on apositional relationship illustrated in the drawings, unless otherwisenoted. Further, a dimensional ratio in the drawings is not intended tolimit the dimensional ratio in the drawings. An acrylate and amethacrylate are collectively referred to as a “(meth)acrylate” in somecases.

A compound according to the present embodiment is a compound representedby Formula (1) given below.

(In the formula, R₁ represents a hydrogen atom or a methyl group,X¹ represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an acryloxy groupor a methacryloxy group, l¹ represents an integer from 0 to 3, Q¹represents a hydrogen atom or Formula (2) given below

(In the formula, R² represents a hydrogen atom or a methyl group,X² represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an acryloxy groupor a methacryloxy group, l² represents an integer from 0 to 3, and *represents a bonding site), andQ² represents a hydrogen atom or Formula (3) given below

(In the formula, R³ represents a hydrogen atom or a methyl group,X³ represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an acryloxy groupor a methacryloxy group, l³ represents an integer from 0 to 3, and *represents a bonding site).)

The compound represented by Formula (1) (hereinafter, referred to as the“compound (1)” in some cases) is a novel compound having a stilbeneskeleton. The compound (1) can be used suitable as one composition of aresin precursor being a material for an optical element or the like.Further, when such compound is used, an optical element having anexcellent θ_(g,F) value can be obtained. Particularly, when suchcompound is used as a material for a multi-layer optical element(cemented lens) obtained by combining a concave lens and a convex lenswith each other, the optical element can exert an excellent opticalcharacteristic while having a thin shape, and an excellent chromaticaberration correction effect can be provided. Note that a θ_(g,F) valueis a value indicated by (n_(g)−n_(F))/(n_(F)−n_(C)) with respect to aC-line (having a wavelength of 656.3 nm), an F-line (having a wavelengthof 486.1 nm), and a g-line (having a wavelength of 435.8 nm) whenrefractive indexes are represented by n_(C), n_(F), and n_(g),respectively.

<Compound (1)>

A structure of the compound (1) is described below.

R₁ represents a hydrogen atom or a methyl group.

X¹ represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylenegroup in which at least one hydrogen is replaced with an (meth)acryloxygroup.

Specific examples of the C_(1 to 9) alkylene group include an ehylenegroup, an n-propylene group, an n-butylene group, a 2-methylpropylenegroup, 1-2-dimethylethylene group, an n-pentylene group, a1,3-dimethylepropylene group, a 2,2-dimethylpropylene group, ann-hexylene group, a 3-methylpentylene group, a 2,3-dimethylbutylenegroup, a 1,2,3-trimethylpropylene group, and a1,1,2,2-tetramethylethylene group. Among those, an ethylene group, ann-propylene group, and a 2,2-dimethylpropylene group are preferred, froma perspective of stability and the like at the time of preparing theresin precursor or the like.

The uppermost number of carbon atoms of the C_(1 to 9) alkylene group ispreferably 5, more preferably, 4. An alkylene group may be linear orbranched.

Specific examples of the C_(3 to 6) alkylene group in which at least onehydrogen is replaced with an acryloxy group or a methacryloxy groupinclude a 2-(meth)acryloxypropylene group, a 3-(meth)acryloxybutylenegroup, a 3-(meth)acryloxypentylene group, and a 4-(meth)acryloxyhexylenegroup. Among those, a 2-(meth)acryloxypropylene group is preferred, froma perspective of stability and the like at the time of preparing theresin precursor or the like. The number of carbon atoms of theC_(3 to 6) alkylene group is preferably 3.

l¹ represents an integer from 0 to 3.

Q¹ represents a hydrogen atom or Formula (2) given below.

Q² represents a hydrogen atom or Formula (3) given below.

R² and R³ independently represent a hydrogen atom or a methyl group.

X² and X³ independently represent a C_(1 to 9) alkylene group, or a C₃to alkylene group in which at least one hydrogen is replaced with an(meth)acryloxy group.

Specific examples of the C_(1 to 9) alkylene group include an ehylenegroup, an n-propylene group, an n-butylene group, a 2-methylpropylenegroup, 1,2-dimethylethylene group, an n-pentylene group, a1,3-dimethylepropylene group, a 2,2-dimethylpropylene group, ann-hexylene group, a 3-methylpentylene group, a 2,3-dimethylbutylenegroup, a 1,2,3-trimethylpropylene group, and a1,1,2,2-tetramethylethylene group. Among those, an ethylene group, ann-propylene group, and a 2,2-dimethylpropylene group are preferred, froma perspective of stability and the like at the time of preparing theresin precursor or the like.

The uppermost number of carbon atoms of the C_(1 to 9) alkylene group ispreferably 5, more preferably, 4. An alkylene group may be linear orbranched.

Specific examples of the C_(3 to 6) alkylene group in which at least onehydrogen is replaced with an acryloxy group or a methacryloxy groupinclude a 2-(meth)acryloxypropylene group, a 3-(meth)acryloxybutylenegroup, a 3-(meth)acryloxypentylene group, and a 4-(meth)acryloxyhexylenegroup. Among those, a 2-(meth)acryloxypropylene group is preferred, froma perspective of stability and the like at the time of preparing theresin precursor or the like. The number of carbon atoms of theC_(3 to 6) alkylene group is preferably 3.

l² and 13 independently represent an integer from 0 to 3.

* represents a bonding site of each of Q¹ and Q².

<Resin Precursor>

According to the present embodiment, a resin precursor containing thecompound (1) and a curable composition can be obtained. The resinprecursor can be used suitably as a resin precursor for an opticalmaterial. When used as an optical material, it is desired that the resinprecursor is stable in a liquid state under an ordinary temperature andpressure. From this perspective, the resin precursor according to thepresent embodiment is preferably in a liquid state under an ordinarytemperature and pressure. Further, when a component described later isused together with the compound (1), deposition of an insolublecomponent can be effectively prevented, and preparation for a stableliquid-state composition can be facilitated.

The curable composition may be photocurable or thermocurable, and ispreferably a photocurable composition. For example, when a large amountof a (meth)acrylate-based compound is contained, a photocurablecomposition is preferred.

The curable composition is not specifically limited. However, forexample, one or more compound selected from a group consisting of afluorine-containing (meth)acrylate compound, a (meth)acrylate compoundhaving a fluorene structure, and a di(meth)acrylate compound may beused. When such component is used together with the compound (1),deposition of an insoluble component can be effectively prevented, andpreparation for a stable liquid composition can be facilitated. As aresult, generation of deposits can be prevented during storage, and anoperation of removing deposits is not required before using thecomposition. A uniformly cured object having a low refractive index andhigh dispersion can be obtained.

A mono-, bi-, tri-, or higher functional fluorine-containing(meth)acrylate is exemplified as a fluorine-containing (meth)acrylatecompound. Among those, a bifunctional fluorine-containing (meth)acrylateis preferred from a perspective of availability. A compound representedby Formula (4) given below is exemplified as a bifunctionalfluorine-containing (meth)acrylate.

(In the formula, R⁴ and R⁵ independently represent a hydrogen atom or amethyl group, Y¹ represents a C_(2 to 12) perfluoroalkylene group, or—(CF₂—O—CF₂)_(z)—, n¹ and n² independently represent an integer from 1to 12, and z represents an integer from 1 to 4.)

R⁴ and R⁵ independently represent a hydrogen atom or a methyl group.Among those, a hydrogen atom is preferred.

Y¹ represents a C_(2 to 12) perfluoroalkylene group or—(CF₂—O—CF₂)_(z)—, and z represents an integer from 1 to 4. Aperfluoroalkylene group may be linear or branched. A perfluoroalkylenegroup is preferably —(CF₂)—, —(CF₂CF₂)—, —(CF₂CF₂CF₂)—, or—(CF₂CF₂CF₂CF₂)—.

n¹ and n² independently represent an integer from 1 to 12. From aperspective of prevention of deposition of an insoluble component at thetime of preparing the resin precursor or the like, and availability, theuppermost value of n¹ and n² is preferably 6, more preferably, 4,further more preferably, 2.

z is preferably an integer from 1 to 3, more preferably, an integer of 1or 2.

Specific examples of a bifunctional fluorine-containing (meth)acrylatecompound include 1,4-di(meth)acryloyloxy-2,2,3,3-tetrafluorobutane,1,6-di(meth)acryloyloxy-3,3,4,4-tetrafluorohexane,1,6-di(meth)acryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane,1,8-di(meth)acryloyloxy-3,3,4,4,5,5,6,6-octafluorooctane,1,8-di(meth)acryloyloxy-2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctane,1,9-di(meth)acryloyloxy-2,2,3,3,4,4,5,5,6,6,7,7,8,8-tetradecafluorononane,1,10-di(meth)acryloyloxy-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecane,and1,12-di(meth)acryloyloxy-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-icosafluorododecane.Further, an ethylene oxide modified fluorinated bisphenol Adi(meth)acrylate, a propylene oxide modified fluorinated bisphenol Adi(meth)acrylate, and the like may be used as a bifunctionalfluorine-containing (meth)acrylate.

Among those, a bifunctional fluorine-containing (meth)acrylate compoundis preferably 1,6-di(meth)acryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane,more preferably, a compound represented by Formula (4-1) given below(1,6-diacryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane).

A content amount of a fluorine-containing (meth)acrylate compound in theresin precursor is not particularly limited. However, from a perspectiveof an optical characteristic such as an abbe number, compatibility withthe compound (1), and the like, the uppermost value of a total amount ofa fluorine-containing (meth)acrylate compound is preferably 50 mass %,more preferably, 45 mass %, further more preferably, 42 mass %. Thelowermost value of the total amount is preferably 20 mass %, morepreferably 30 mass %, further more preferably, 35 mass %.

Examples of a (meth)acrylate compound having a fluorene structureinclude a monofunctional (meth)acrylate compound having a fluorenestructure, a bifunctional(meth)acrylate compound having a fluorenestructure, and a tri- or higher functional (meth)acrylate compoundhaving a fluorene structure. Among those, a bifunctional(meth)acrylatecompound having a fluorene structure is preferred from a perspective ofavailability. Specific examples of such compound include a compoundrepresented by Formula (5) given below and a compound represented byFormula (6) given below.

(In the formula, R⁶ and R⁷ independently represent a hydrogen atom or amethyl group, R⁸ and R⁹ independently represent a hydrogen atom, amethyl group, or an ethyl group, R¹⁰, R₁₁, R¹², and R¹³ independentlyrepresent a hydrogen atom, a fluorine atom, a C_(1 to 6) alkyl group, ora phenyl group in which a hydrogen atom may be replaced with a fluorineatom or a C_(1 to 6) alkyl group, and n³ and n⁴ independently representan integer from 0 to 3.)

(In the formula, R¹⁴ represents a hydrogen atom or a methyl group, R¹⁵and R¹⁶ independently represent a hydrogen atom, a methyl group, or anethyl group, R¹⁷, R¹⁸, R¹⁹, and R²⁰ independently represent a hydrogenatom, a fluorine atom, a C_(1 to 6) alkyl group, or a phenyl group inwhich a hydrogen atom may be replaced with a fluorine atom or aC_(1 to 6) alkyl group, n⁵ and n⁶ independently represent an integerfrom 0 to 3.)

Formula (5) is described.

R⁶ and R⁷ independently represent a hydrogen atom or a methyl group.Among those, a hydrogen atom is preferred.

R⁸ and R⁹ independently represent a hydrogen atom, a methyl group, or anethyl group. Among those, from a perspective of availability, a hydrogenatom is preferred.

R¹⁰, R¹¹, R¹² and R¹³ independently represent a hydrogen atom, afluorine atom, a C_(1 to 6) alkyl group, or a phenyl group in which ahydrogen atom may be replaced with a fluorine atom or a C_(1 to 6) alkylgroup.

As a C_(1 to 6) alkyl group, a linear, branched, or cyclic alkyl groupmay be provided. From a perspective of availability, a linear or abranched alkyl group is preferred. Specific examples of a C_(1 to 6)alkyl group include a methyl group, an ethyl group, an n-propyl group,an isopropyl group, an n-butyl group, an isobutyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, ann-hexyl group, an isohexyl group, a neohexyl group, a cyclopropyl group,a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Amongthose, a methyl group and an ethyl group are preferred.

A phenyl group in which a hydrogen atom may be replaced with a fluorineatom or a C_(1 to 6) alkyl group is obtained by replacing part or anentirety of a hydrogen atom in a phenyl group with a fluorine atom or aC_(1 to 6) alkyl group. As a C_(1 to 6) alkyl group as described above,a methyl group and an ethyl group are preferred from a perspective ofavailability.

n³ and n⁴ independently represent an integer from 0 to 3. Among those,n³ and n⁴ are preferably an integer from 0 to 2, more preferably, 0 or1, further more preferably, 1, from a perspective of high hardness andtransparency, and an excellent optical characteristic.

Formula (6) is described.

R¹⁴ represents a hydrogen atom or a methyl group. Among those, ahydrogen atom is preferred.

R¹⁵ and R¹⁶ independently represent a hydrogen atom, a methyl group, oran ethyl group. Among those, from a perspective of availability, ahydrogen atom is preferred.

R¹⁷, R¹⁸, R¹⁹ and R²⁰ independently represent a hydrogen atom, afluorine atom, a C_(1 to 6) alkyl group, or a phenyl group in which ahydrogen atom may be replaced with a fluorine atom or a C_(1 to 6) alkylgroup.

As a C_(1 to 6) alkyl group, a linear, branched, or cyclic alkyl groupmay be provided. From a perspective of availability, a linear or abranched alkyl group is preferred. Specific examples of a C_(1 to 6)alkyl group include a methyl group, an ethyl group, an n-propyl group,an isopropyl group, an n-butyl group, an isobutyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, ann-hexyl group, an isohexyl group, a neohexyl group, a cyclopropyl group,a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Amongthose, a methyl group and an ethyl group are preferred.

A phenyl group in which a hydrogen atom may be replaced with a fluorineatom or a C_(1 to 6) alkyl group is obtained by replacing part or anentirety of a hydrogen atom in a phenyl group with a fluorine atom or aC_(1 to 6) alkyl group. As such a phenyl group in which a hydrogen atommay be replaced with a C_(1 to 6) alkyl group described above, a phenylgroup, a methylphenyl group, an ethylphenyl group are preferred from aperspective of availability.

n⁵ and n⁶ independently represent an integer from 0 to 3. Among those,n⁵ and n⁶ are preferably an integer from 0 to 2, more preferably, 0 or1, further more preferably, 1, from a perspective of high hardness andtransparency, and an excellent optical characteristic.

Specific examples of a (meth)acrylate compound having a fluorenestructure preferably include a compound represented by Formula (5-1)given below and a compound represented by Formula (6-1) given below,more preferably, a compound(9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene) represented by Formula(5-1) given below.

A content amount of a (meth)acrylate compound having a fluorenestructure in the resin precursor is not particularly limited. However,from a perspective of prevention of white turbidity and prevention ofdeposition of an insoluble component, a total amount of a (meth)acrylatecompound having a fluorene structure is preferably 20 to 50 mass %. Theuppermost content amount is more preferably 40 mass %, further morepreferably, 35 mass %. The lowermost content amount is more preferably25 mass %, further more preferably, 26 mass %.

As a di(meth)acrylate compound other than each component describedabove, a compound having two (meth)acrylate structures is exemplified.Specific examples of a di(meth)acrylate compound include a2-ethyl-2-butyl-propanediol(meth)acrylate, a1,3-butyleneglycoldi(meth)acrylate, a 1,6-hexanedioldi(meth)acrylate, a1,9-nonanediol(meth)acrylate, a 1,10-decanedioldi(meth)acrylate, aneopentylglycoldi(meth)acrylate, a dipropyleneglycoldi(meth)acrylate, aglyceroldi(meth)acrylate, an ethylene oxide modifiedneopentylglycoldi(meth)acrylate, a propylene oxide modifiedneopentylglycoldi(meth)acrylate, an ethylene oxide modified bisphenol Adi(meth)acrylate, a propylene oxide modified bisphenol Adi(meth)acrylate, an ethylene oxide/propylene oxide modified bisphenol Adi(meth)acrylate, and a butylethylpropanedioldi(meth)acrylate.

Among those di(meth)acrylate compounds, an aliphatic di(meth)acrylate ispreferred, from a perspective of compatibility with the compound (1) andthe like. Among those, a 2-ethyl-2-butyl-propanediol(meth)acrylate, a1,3-butyleneglycoldi(meth)acrylate, and a 1,6-hexanedioldi(meth)acrylateare preferred, and 1,6-hexanediol diacrylate (AHDN) is preferred more.An aliphatic di(meth)acrylate has a chemical structure that achieveshigh compatibility with the compound (1), and hence a stable liquidstate can be maintained. As a result, the resin precursor in a liquidstate, which contains the compound (1) in high concentration can beachieved. When used as an optical material, the resin precursorcontaining the compound (1) in high concentration can further exert aneffect relating to an optical characteristic.

A content amount of a di(meth)acrylate compound in the resin precursoris not particularly limited. However, from a perspective ofcompatibility with the compound (1) and the like, a total amount of adi(meth)acrylate compound is preferably 10 to 80 mass %. The uppermostcontent amount is more preferably 60 mass %, further more preferably, 50mass %. The lowermost content amount is more preferably 20 mass %,further more preferably, 35 mass %.

The curable composition according to the present embodiment may containa component other than those described above. A monofunctional(meth)acrylate, a trifunctional (meth)acrylate, and a tetrafunctional(meth)acrylate are exemplified. By using those together, hardness,transparency, and an optical characteristic of the resin can beadjusted. Among those, a monofunctional (meth)acrylate is preferred,from a perspective of improving compatibility with the compound (1).

Examples of a monofunctional (meth)acrylate include amethyl(meth)acrylate, ethyl(meth)acrylate, a butyl(meth)acrylate, anisodecyl(meth)acrylate, a lauryl(meth)acrylate, atridecyl(meth)acrylate, an acetyl(meth)acrylate, astearyl(meth)acrylate, a tert-butyl(meth)acrylate, a2-ethylhexyl(meth)acrylate, a 2-hydroxybutyl(meth)acrylate, a2-hydroxyethyl(meth)acrylate, a 2-hydroxypropyl(meth)acrylate, a3-methoxybutyl(meth)acrylate, a diethylaminoethyl(meth)acrylate, aphenoxypolyethyleneglycol(meth)acrylate, an isostearyl(meth)acrylate, aparacumylphenoxyethyleneglycol(meth)acrylate, adimethylaminoethyl(meth)acrylate, a 2-ethylhexylcarbitol(meth)acrylate,a butoxyethyl(meth)acrylate, an ethoxydiethyleneglycol(meth)acrylate, alauroxypolyethyleneglycol(meth)acrylate, apolyethyleneglycol(meth)acrylate, a methoxydipropyleneglycolacrylate, amethoxytrypropyleneglycolacrylate, an ethoxydipropyleneglycolacrylate,an ethoxytrypropyleneglycolacrylate, apolypropyleneglycol(meth)acrylate, anacryloxypolyethyleneglycol(meth)acrylate, astearoxypolyethyleneglycol(meth)acrylate, anoctoxypolyethyleneglycol-polypropyleneglycol(meth)acrylate, apoly(propyleneglycol-tetramethyleneglycol) (meth)acrylate, apoly(ethyleneglycol-tetramethyleneglycol) (meth)acrylate, amethoxypolyethyleneglycol(meth)acrylate, amethoxypolypropyleneglycol(meth)acrylate, and a benzil(meth)acrylate.Among those, methoxytrypropyleneglycolacrylate andethoxytrypropyleneglycolacrylate are preferred, from a perspective of astructure regarding compatibility with the compound (1) and the like.

Examples of a trifunctional(meth)acrylate includes atris(acryloxyethyl)isocyanurate, a tris(methacryloxyethyl) isocyanurate,an epichlorohydrin modified glyceroltri(meth)acrylate, an ethylene oxidemodified glyceroltri(meth)acrylate, a propylene oxide modifiedglyceroltri(meth)acrylate, a caprolactone modifiedtrimethylolpropanetri(meth)acrylate, an ethylene oxide modifiedtrimethylolpropanetri(meth)acrylate, a propylene oxide modifiedtrimethylolpropanetri(meth)acrylate, a pentaerythritoltri(meth)acrylate,and a trimethylolpropanetri(meth)acrylate. Among those, apentaerythritoltri(meth)acrylate is preferred, from a perspective of astructure regarding compatibility with the compound (1) and the like.

As a tetrafunctional (meth)acrylate, a pentaerythritoltetra(meth)acrylate, a dipentaerythritol hydroxypenta(meth)acrylate, anda ditrimethylolpropane tetra(meth)acrylate are exemplified. Among those,a dipentaerythritol hydroxypenta(meth)acrylate is preferred, from aperspective of a structure regarding compatibility with the compound (1)and the like.

When the resin precursor according to the present embodiment isphotocurable, the resin precursor may further contain aphotopolymerization initiator. The photopolymerization initiator is notparticularly limited as long as polymerization of monomeric componentscan be initiated with light irradiation, and a publicly-knownphotopolymerization initiator used for photo-curing a resin may be used.Light used for light irradiation may be selected as appropriate inaccordance with a photopolymerization initiator to be used, and visiblelight, ultraviolet light, an electron beam, and the like are generallyused.

A content amount of the photopolymerization initiator depends on a typeof used components or a type of irradiation light, and, in general, ispreferably 0.1 to 5 mass %.

As the photopolymerization initiator, for example, a phosphine-based oracetophenone-based photopolymerization initiator is preferred, from aperspective of reactivity. As a phosphine-based photopolymerizationinitiator, a bis(2-4-6-trimethylbenzoyl)-phenylphosphineoxide, a2,4,6-trimethylbenzoyl-diphenyl-phosphineoxide, and the like arepreferred. As an acetophenone-based photopolymerization initiator,alkylphenyl ketones having a hydroxyl group at the alpha-position arepreferred, and a 1-hydroxy-cyclohexyl-phenyl-ketone, a2-hydroxy-2-methyl-1-phenyl-propane-1-one, and the like are morepreferred, from a perspective of prevention of yellowing of a resin inaddition to a perspective of reactivity.

The resin precursor according to the present embodiment may furthercontain a photostabilizer. A publicly-known photostabilizer may be usedas the photostabilizer. Suitable examples of the photostabilizer includea hindered amine based material such as abis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, abis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, and amethyl-1,2,2,6,6-pentamethyl-4-piperidylsebacate.

The resin precursor according to the present embodiment may furthercontain a polymerization-inhibitor. A publicly-knownpolymerization-inhibitor may be used as the polymerization-inhibitor.Suitable examples of the polymerization-inhibitor include hydroquinonessuch as a p-benzoquinone, a hydroquinone, a hydroquinonemonomethylether,and a 2,5-diphenylparabenzoquinone, substituted catechols such as aT-butyl catechol, a phenothiazine, amines such as a diphenylamine, N-oxyradicals such as a tetramethylpiperidinyl-N-oxy radical (TEMPO), anitrosobenzene, a picric acid, molecular oxygen, and sulfur. Amongthose, hydroquinones, a phenothiazine, and N-oxy radicals are morepreferred, from a perspective of versatility and prevention ofpolymerization.

The resin precursor according to the present embodiment may furthercontain an ultraviolet light absorber. A publicly-known ultravioletlight absorber may be used as the ultraviolet light absorber. Suitableexamples include a 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole.When used together with the photostabilizer, the ultraviolet lightabsorber can be expected to exert a further excellent effect.

As suitable combinations of the components described above for thecurable composition that is used together with the compound (1), thecurable composition preferably contain a fluorine-containing(meth)acrylate compound or a (meth)acrylate compound having a fluorenestructure, and a di(meth)acrylate compound, more preferably, afluorine-containing (meth)acrylate compound and a di(meth)acrylatecompound, further more preferably, an aliphatic fluorine-containing(meth)acrylate compound and an aliphatic di(meth)acrylate compound.

As a specific component combination of the suitable combinationsdescribed above, the curable composition preferably contains any oneselected from a group consisting of a9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, amethoxytrypropyleneglycolacrylate, a1,6-di(meth)acryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane, a1-hydroxy-cyclohexyl-phenyl-ketone, abis(2-4-6-trimethylbenzoyl)-phenylphosphineoxide, abis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, a methyl1,2,2,6,6-pentamethyl-4-piperidylsebacate, a2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, and a 1,6-hexanedioldiacrylate.

Among those, it is more preferred that one or more kinds selected from agroup consisting of a1,6-di(meth)acryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane, a9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, and a 1,6-hexanedioldiacrylate be contained, from a perspective of effective prevention ofdeposition of an insoluble component and easy preparation for a stableliquid-state composition. Further, it is further more preferred that twoor more kinds selected from a group consisting of a1,6-di(meth)acryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane, a9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, and a 1,6-hexanedioldiacrylate be contained. Further, it is further more preferred that a1,6-di(meth)acryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane, a9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, and a 1,6-hexanedioldiacrylate be contained. When such component is used together with thecompound (1), preparation is further facilitated to obtain aliquid-state composition having high stability under an ordinarytemperature.

A content amount of the compound (1) in the resin precursor is notparticularly limited. However, from a perspective of maintaining highstability in a liquid state, the content amount is preferably 10 to 90mass %. From the perspective described above, the uppermost contentamount is more preferably 50 mass %, further more preferably, 30 mass %,still further more preferably, 25 mass %. The lowermost content amountis more preferably 15 mass %.

<Cured Object>

A cured object can be obtained by curing the resin precursor accordingto the present embodiment. A curing method may be photocuring orthermocuring, depending on a property of the contained curablecomposition. As the curing method, for example, a method of using anultraviolet-light curable composition and performing irradiation ofultraviolet light may be employed.

As a physical property of the cured object, a θ_(g,F) value ispreferably 0.5 or greater, more preferably, 0.6 or greater, further morepreferably, 0.7 or greater. The lowermost value of an abbe number(ν_(d)) is preferably 10 or greater, more preferably, 15 or greater,further more preferably, 17 or greater. The uppermost value of an abbenumber (ν_(d)) is preferably 40 or less, more preferably, 30 or less,further more preferably, 27 or less. A numerical range of an abbe number(ν_(d)) is preferably 10 or greater and 40 or less. Further, it ispreferred that both the θ_(g,F) value and the abbe number (ν_(d))respectively satisfy the numerical ranges described above. A refractiveindex (n_(d)) with respect to a d-line may be 1.50 or greater and 1.65or less.

A glass material and an optical material formed of an organic resin orthe like have a tendency of reducing a refractive index as approaching asmall wavelength side. As an index indicating a wavelength dispersioncharacteristic of a refractive index, the θ_(g,F) value and the abbenumber (ν_(d)) are used. These values are unique to optical materials.In a refraction optical system, reduction in chromatic aberration hasbeen attempted by appropriately combining optical materials havingdifferent dispersion characteristics. However, when the configuration orthe number of lenses is limited from a perspective of design requirementor the like, it is difficult to correct chromatic aberrationsufficiently in some cases. In view of this, the cured object accordingto the present embodiment has a high θ_(g,F) value, and has a uniquedispersion characteristic. The cured object according to the presentembodiment has such property, and hence has an excellent chromaticaberration correction function. Thus, such problem can be solved.

Further, an inner transmittance of the cured object is preferably 80% orgreater over a wavelength range from 440 nm to 500 nm. A wavelength(λ₈₀) at which an inner transmittance is 80% is preferably 430 nm orless, more preferably, 420 nm or less, further more preferably, 410 nmor less. According to the present embodiment, the cured object having ahigh inner transmittance can be obtained as an optical material.

<Optical Element, Optical System, Interchangeable Camera Lens, OpticalDevice, and the Like>

The cured object according to the present embodiment may be used as anoptical element. The optical element including the cured object includesa mirror, a lens, a prism, and a filter. Suitable usage examples includean optical lens. Further, the optical element according to the presentembodiment may be used for an optical system including the opticalelement.

The optical system according to the present embodiment may be suitablyused for an interchangeable camera lens including the optical system.Publicly-known configurations may be employed for the optical element,the optical lens, and the interchangeable camera lens. Further, theoptical system according to the present embodiment may be suitably usedfor an optical device including the optical system. The optical deviceincluding the optical system is not particularly limited, and examplesthereof include an imaging device such as a lens-interchangeable cameraand a fixed lens camera, and an optical microscope.

(Imaging Device)

FIG. 1 is a perspective view of one example of an optical deviceaccording to the present embodiment as an imaging device.

An imaging device 1 is a so-called digital single-lens reflex camera (alens-interchangeable camera), and a photographing lens (an opticalsystem) 103 includes the cured object according to the presentembodiment. A lens barrel 102 is mounted to a lens mount (notillustrated) of a camera body 101 in a removable manner. Further, animage is formed with light, which passes through the lens 103 of thelens barrel 102, on a sensor chip (solid-state imaging elements) 104 ofa multi-chip module 106 arranged on a back surface side of the camerabody 101. The sensor chip 104 is a so-called bare chip such as a CMOSimage sensor, and the multi-chip module 106 is, for example, a Chip OnGlass (COG) type module including the sensor chip 104 being a bare chipmounted on a glass substrate 105.

FIG. 2 is a front view of another example of the optical deviceaccording to the present embodiment as an imaging device. FIG. 3 is aback view of the imaging device.

The imaging device CAM is a so-called digital still camera (a fixed lenscamera), and a photographing lens (an optical system) WL includes thecured object according to the present embodiment. When a power button(not illustrated) of the imaging device CAM is pressed, a shutter (notillustrated) of the photographing lens WL is opened, light from anobject to be imaged (a body) is converged by the photographing lens WLand forms an image on imaging elements arranged on an image surface. Anobject image formed on the imaging elements is displayed on a liquidcrystal monitor M arranged on the back of the imaging device CAM. Aphotographer decides composition of the object image while viewing theliquid crystal monitor M, then presses down a release button B1, andcaptures the object image on the imaging elements. The object image isrecorded and stored in a memory (not illustrated). For example, anauxiliary light emitting unit EF that emits auxiliary light in a casethat the object is dark and a function button B2 to be used for settingvarious conditions of the imaging device CAM and the like are arrangedon the imaging device CAM.

A higher resolution, lighter weight, and a smaller size are demanded forthe optical system to be used in such digital camera or the like. Inorder to achieve such demands, it is effective to use optical glass witha high refractive index as the optical system. From such viewpoint, theoptical glass according to the present embodiment is suitable as amember of such optical device. Note that, in addition to the imagingdevice described above, examples of the optical device to which thepresent embodiment is applicable include a projector and the like. Inaddition to the lens, examples of the optical element include a prism.

(Multi-Photon Microscope)

FIG. 4 is a block diagram illustrating one example of the optical deviceaccording to the present embodiment as a multi-photon microscope.

The multi-photon microscope 2 includes an objective lens 206, acondensing lens 208, and an image forming lens 210, as optical elements.Hereinafter, description is mainly made on the optical system of themulti-photon microscope 2.

A pulse laser device 201 emits ultrashort pulse light having, forexample, a near infrared wavelength (approximately 1,000 nm) and a pulsewidth of a femtosecond unit (for example, 100 femtoseconds). In general,ultrashort pulse light immediately after being emitted from the pulselaser device 201 is linearly polarized light that is polarized in apredetermined direction.

A pulse division device 202 divides the ultrashort pulse light,increases a repetition frequency of the ultrashort pulse light, andemits the obtained light.

A beam adjustment unit 203 has a function of adjusting a beam diameterof the ultrashort pulse light, which enters from the pulse divisiondevice 202, to a pupil diameter of the objective lens 206, a function ofadjusting convergence and divergence angles of the ultrashort pulselight in order to correct chromatic aberration (a focus difference) onan axis of a wavelength of multi-photon excitation light emitted from asample S and the wavelength of the ultrashort pulse light, a pre-chirpfunction (group velocity dispersion compensation function) providinginverse group velocity dispersion to the ultrashort pulse light in orderto correct increased of the pulse width of the ultrashort pulse lightdue to group velocity dispersion at the time of passing through theoptical system, and the like.

The ultrashort pulse light emitted from the pulse laser device 201 has arepetition frequency increased by the pulse division device 202, and isadjusted as mentioned above by the beam adjustment unit 203.Furthermore, the ultrashort pulse light emitted from the beam adjustmentunit 203 is reflected on a dichroic mirror 204 in a direction toward adichroic mirror 205, passes through the dichroic mirror 205, isconverged by the objective lens 206, and is radiated to the sample S. Atthis time, an observation surface of the sample S may be scanned withthe ultrashort pulse light through use of a scanning means (notillustrated).

For example, when the sample S is subjected to fluorescence imaging, afluorescent pigment by which the sample S is dyed is subjected tomulti-photon excitation in an irradiated region with the ultrashortpulse light and the vicinity thereof on the sample S, and fluorescencehaving a wavelength shorter than an infrared wavelength of theultrashort pulse light (hereinafter, also referred to “observationlight”) is emitted.

The observation light emitted from the sample S in a direction towardthe objective lens 206 is collimated by the objective lens 206, and isreflected on the dichroic mirror 205 or passes through the dichroicmirror 205 depending on the wavelength.

The observation light reflected on the dichroic mirror 205 enters afluorescence detection unit 207. The fluorescence detection unit 207 isformed of, for example, a barrier filter, a photo multiplier tube (PMT),or the like, receives the observation light reflected on the dichroicmirror 205, and outputs an electronic signal depending on an amount ofthe light. The fluorescence detection unit 207 detects the observationlight over the observation surface of the sample S, in conformity withthe ultrashort pulse light scanning on the observation surface of thesample S.

Meanwhile, the observation light passing through the dichroic mirror 205is de-scanned by a scanning means (not illustrated), passes through thedichroic mirror 204, is converged by the condensing lens 208, passesthrough a pinhole 209 provided at a position substantially conjugate toa focal position of the objective lens 206, passes through the imageforming lens 210, and enters a fluorescence detection unit 211.

The fluorescence detection unit 211 is formed of, for example, a barrierfilter, a PMT, or the like, receives the observation light forming animage on a reception surface of the fluorescence detection unit 211 bythe image forming lens 210, and outputs an electronic signal dependingon an amount of the light. The fluorescence detection unit 211 detectsthe observation light over the observation surface of the sample S, inconformity with the ultrashort pulse light scanning on the observationsurface of the sample S.

Note that, all the observation light emitted from the sample S in adirection toward the objective lens 206 may be detected by thefluorescence detection unit 211 by excluding the dichroic mirror 205from the optical path.

The observation light emitted from the sample S in a direction oppositeto the objective lens 206 is reflected on a dichroic mirror 212, andenters a fluorescence detection unit 213. The fluorescence detectionunit 213 is formed of, for example, a barrier filter, a PMT, or thelike, receives the observation light reflected on the dichroic mirror212, and outputs an electronic signal depending on an amount of thelight. The fluorescence detection unit 213 detects the observation lightover the observation surface of the sample S, in conformity with theultrashort pulse light scanning on the observation surface of the sampleS.

The electronic signals output from the fluorescence detection units 207,211, and 213 are input to, for example, a computer (not illustrated).The computer is capable of generating an observation image, displayingthe generated observation image, storing data on the observation image,based on the input electronic signals.

<Cemented Lens and Method for Manufacturing Cemented Lens>

A case where the compound, the resin precursor, and the cured objectaccording to the present embodiment are used for a single lens is mainlydescribed above. The compound, the resin precursor, the cured object andthe like according to the present embodiment may be suitably used as ajoining member of a cemented lens including a plurality of lenses.

FIG. 5 is a schematic view illustrating one example of the cemented lensaccording to the present embodiment.

A cemented lens 3 includes a first lens element 301 and a second lenselement 302 joined with each other through intermediation of the curedobject 303 according to the present embodiment. Note that, the lensesforming the cemented lens are referred to as “lens elements” asdescribed above in some cases from a viewpoint of clearly stating thatthe lenses are the elements of the cemented lens. In this manner, thecured object 303 according to the present embodiment can be caused tofunction as the joining member described above.

When the compound, the resin precursor, and the cured object accordingto the present embodiment are used for a cemented lens including twolens elements, there is exemplified a manufacturing method including,firstly, (1) a contacting step of contacting the first lens element andthe second lens element with each other through intermediation of theresin precursor according to the present embodiment, and (2) a joiningstep of curing the resin precursor to join the first lens element andthe second lens element with each other.

(1) In the contacting step, the resin precursor according to the presentembodiment is interposed in a pre-cured state between the first lenselement and the second lens element. For example, when the resinprecursor is a liquid-state composition, the resin precursor is appliedon contact surfaces between the first lens element and the second lenselement, and both the lens elements are laid over with each other.

(2) In the joining step, a method of curing the resin precursor may bephotocuring or thermocuring. Curing is performed preferably byirradiating the resin precursor with light. The resin precursor ispreferably irradiated with light through the first lens element or thesecond lens element. The compound, the resin precursor, and the curedobject according to the present embodiment can prevent yellowing due toaging, and can maintain high transparency for a long period of time.From this perspective, the manufacturing method is suitable.

The cementing lens thus obtained may be used for an optical system,similarly as described with the single lens. The cemented lens accordingto the present embodiment may be suitably used for an optical deviceincluding an interchangeable camera lens and an optical system,similarly as described with the single lens. Note that, in the aspectdescribed above, description is made on the cemented lens using the twolens elements. The present invention is however not limited thereto, anda cemented lens using three or more lens elements may be used. When acemented lens using three or more lens elements is obtained, the curedobject according to the present embodiment may be applied to all thejoining members between the lens elements. However, the presentinvention is not limited thereto, and the cured object according to thepresent embodiment is only required to be applied to at least one of thejoining members.

EXAMPLES

The present invention is further described in detail with Examples andComparative Examples given below. However, the following examples arenot intended to limit the present invention at all. First, compoundswere synthesized, resin precursors containing those compounds and curedobjects obtained therefrom were produced, and physical propertyevaluation was performed on each resultant.

I. Production of Compound and Physical Property Evaluation Example 1(Synthesis of Compound (1A))

(Synthesis of Intermediate Compound (a1))

10.00 g (49.7 mmol) of 4-bromobenzoic acid, 15.54 g (149.2 mmol) of2,2-dimethyl-1,3-propanediol, and 200 mL of tetrahydrofuran(dehydration) were measured and put in a reactor vessel, and theresultant was stirred to obtain a uniform solution. 11.44 g (59.7 mmol)of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride and 304mg (2.49 mmol) of 4-dimethylaminopyridine were added to the resultantand it became a suspension. Stirring was performed at a room temperaturefor one night. After that, when the reaction solution was checked withthin layer chromatography (TLC), it was found that 4-bromobenzoic aciddisappeared. The reaction solution was concentrated under a low pressureat a temperature of 40 degrees Celsius, and then 100 mL of ethyl acetatewere added. The resultant was replaced in a separating funnel, and waswashed twice with 100 mL of a saturated saline solution. The resultantwas replaced in another vessel, and anhydrous magnesium sulfate wasadded.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The colorless liquid obtained through refining with a silicagel column (a development solvent satisfied n-hexane:ethyl acetate=3:1),was dried under a low pressure at a temperature of 70 degrees Celsiusfor three hours. Thus, an intermediate compound (a1) was obtained as awhite solid. The yield amount was 9.40 g (32.8 mmol), and the yield was65.8%.

(Synthesis of Intermediate Compound (a2))

9.40 g (32.8 mmol) of the intermediate compound (a1), 9.79 g (42.6 mmol)of trans-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene, and 120mL of dioxane were measured and put in a reactor vessel, and theresultant was stirred while subjecting to ultrasonic waves to obtain auniform solution. A dilute solution of 13.53 g (127.7 mmol) of sodiumhydrogen carbonate with 60 ml of pure water and 757 mg (0.655 mmol) of atetrakis(triphenylphosphine)palladium(0) complex were added to theresultant. While water at a temperature of 5 degrees Celsius was causedto flow through a cooling tube, the resultant was stirred at atemperature of 110 degrees Celsius for four hours. After that, when thereaction solution was checked with TLC, it was found that theintermediate compound (a1) disappeared. At this point, 80 mL of a 2Nammonium chloride aqueous solution were added to the reaction solution.The resultant was separated into an organic layer and a water layer by aseparating funnel, and then the water layer was extracted twice by 30 mLof ethyl acetate. The organic layer and the extracted layer werecollectively washed twice with 100 mL of a saturated saline solution.The resultant was replaced in another vessel, and anhydrous magnesiumsulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degrees ofCelsius. 30 mL of n-hexane and 15 mL of ethyl acetate were added, andthe resultant was stirred at a temperature of 50 degrees Celsius toobtain a uniform solution. When being left at a room temperature for onenight, white crystals were precipitated, which were recovered throughfiltration and dried under a low pressure at a temperature of 70 degreesCelsius for four hours. Thus, an intermediate compound (a2) wasobtained. The yield amount was 6.37 g (20.5 mmol), and the yield was62.7%.

(Synthesis of Target Compound (1A))

6.37 g (20.5 mmol) of the intermediate compound (a2), 5.19 g (51.3 mmol)of triethylamine (Et₃N), 127 mg (1.02 mmol) of 4-methoxyphenol (MEHQ),and 80 mL of tetrahydrofuran (dehydration) were measured and put in areactor vessel. The resultant was stirred to obtain a uniform solution,and was cooled to a temperature of 0 degrees Celsius. 4.29 g (41.0 mmol)of methacryloyl chloride were slowly dropped to the resultant. Stirringwas sequentially performed for two hours. After that, when the reactionsolution was checked with TLC, it was found that the intermediatecompound (a2) almost disappeared. At this point, 80 mL of a 2N sodiumhydroxide aqueous solution were added to the reaction solution. Theresultant was separated into an organic layer and a water layer by aseparating funnel, and then the water layer was extracted twice by 20 mLof ethyl acetate. The organic layer and the extracted layer werecollectively washed twice with 100 mL of a saturated saline solution.The resultant was replaced in another vessel, and anhydrous magnesiumsulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 40 degreesCelsius. 2 mL of a chloroform solution with 1 mg/mL of MEHQ were addedto the slightly yellow-colored liquid obtained through refining with asilica gel column (a development solvent satisfied n-hexane:ethylacetate=3:1), and the resultant was dried under a low pressure at atemperature of 40 degrees Celsius for three hours. Thus, a targetcompound (1A) was obtained as a white solid (melting point: 64° C.). Theyield amount was 7.48 g (19.8 mmol), and the yield was 96.4%.

Measurement results of 1H-NMR (“AVANCE III HD” available from Bruker)being the compound (1A) are shown below.

¹H-NMR (500 MHz, DMSO-d6): δ1.05 (6H, s), 1.88 (3H, s), 4.03 (2H, s),4.13 (2H, s), 5.67 (1H, s), 6.06 (1H, s), 7.30-7.44 (5H, m), 7.64-7.66(2H, d), 7.74-7.76 (2H, d), 7.96-7.98 (2H, d)

Example 2 (Synthesis of Compound (1B))

(Synthesis of Intermediate Compound (b1))

5.00 g (24.9 mmol) of 4-bromobenzoic acid, 3.94 g (29.8 mmol) of2,2-dimethyl-1,3-dioxolane-4-methanol, and 100 mL of tetrahydrofuran(dehydration) were measured and put in a reactor vessel, and theresultant was stirred to obtain a uniform solution. 5.72 g (29.8 mmol)of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride and 152mg (2.49 mmol) of 4-dimethylaminopyridine were added to the resultantand it became a suspension. Stirring was performed at a room temperaturefor one night. After that, when the reaction solution was checked withTLC, it was found that 4-bromobenzoic acid disappeared. The reactionsolution was concentrated under a low pressure at a temperature of 40degrees Celsius, and then 50 mL of ethyl acetate were added.

Insoluble matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The colorless liquid obtained through refining with a silicagel column (a development solvent satisfied n-hexane:ethyl acetate=3:1)was dried under a low pressure at a temperature of 70 degrees Celsiusfor three hours. Thus, an intermediate compound (b1) was obtained as awhite solid. The yield amount was 5.88 g (18.7 mmol), and the yield was75.0%.

(Synthesis of Intermediate Compound (b2))

5.88 g (18.7 mmol) of the intermediate compound (b1), 5.58 g (24.3 mmol)of trans-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene, and 100mL of dioxane were measured and put in a reactor vessel, and theresultant was stirred while subjecting to ultrasonic waves to obtain auniform solution. A dilute solution of 7.71 g (72.8 mmol) of sodiumhydrogen carbonate with 50 ml of pure water, and 431 mg (0.373 mmol) ofa tetrakis(triphenylphosphine)palladium(0) complex were added to theresultant. While water at a temperature of 5 degrees Celsius was causedto flow through a cooling tube, the resultant was stirred at atemperature of 110 degrees Celsius for three hours. After that, when thereaction solution was checked with TLC, it was found that theintermediate compound (b1) disappeared. At this point, 70 mL of a 2Nammonium chloride aqueous solution were added to the reaction solution.The resultant was separated into an organic layer and a water layer by aseparating funnel, and then the water layer was extracted twice by 20 mLof 2-methyltetrahydrofuran. The organic layer and the extracted layerwere collectively washed twice with 100 mL of a saturated salinesolution. The resultant was replaced in another vessel, and anhydrousmagnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The light yellow-colored solid matters obtained throughrefining with a silica gel column (a development solvent satisfiedn-hexane:ethyl acetate=3:1) was dried under a low pressure at atemperature of 70 degrees Celsius for three hours. Thus, an intermediatecompound (b2) was obtained. The yield amount was 2.57 g (7.59 mmol), andthe yield was 47.0%.

(Synthesis of Intermediate Compound (b3))

2.57 g (7.59 mmol) of the intermediate compound (b2) and 25 mL of2-methyltetrahydrofuran were measured and put in a reactor vessel, andthe resultant was stirred while subjecting to ultrasonic waves to obtaina uniform solution. After that, 1 mL (12 mmol) of 12N hydrochloric acidwere slowly dropped to the resultant while stirring. Stirring wasperformed at a room temperature for one night. After that, when thereaction solution was checked with TLC, it was found that theintermediate compound (b2) disappeared. At this point, 1.22 g (12 mmol)of triethylamine (Et₃N) and anhydrous magnesium sulfate were added tothe reaction solution.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The white solid matters obtained through refining with a silicagel column (a development solvent satisfied n-hexane:ethyl acetate=1:99)was dried under a low pressure at a temperature of 70 degrees Celsiusfor three hours. Thus, an intermediate compound (b3) was obtained. Theyield amount was 1.71 g (5.73 mmol), and the yield was 75.5%.

(Synthesis of Target Compound (1B))

1.71 g (5.73 mmol) of the intermediate compound (b3), 2.03 g (20.1 mmol)of triethylamine (Et₃N), 34 mg (0.28 mmol) of 4-methoxyphenol (MEHQ),and 20 mL of tetrahydrofuran (dehydration) were measured and put in areactor vessel. The resultant was stirred while subjecting to ultrasonicwaves to obtain a uniform solution, and then cooled to a temperature of0 degrees Celsius. 1.80 g (17.2 mmol) of methacryloyl chloride wereslowly dropped to the resultant. Stirring was sequentially performed forthree hours. After that, when the reaction solution was checked withTLC, it was found that the intermediate compound (b3) disappeared. Atthis point, 20 mL of a 2N sodium hydroxide aqueous solution were addedto the reaction solution. The resultant was separated into an organiclayer and a water layer by a separating funnel, and then the water layerwas extracted twice by 10 mL of ethyl acetate. The organic layer and theextracted layer were collectively washed twice with 30 mL of a saturatedsaline solution. The resultant was replaced in another vessel, andanhydrous magnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 40 degreesCelsius. 0.5 mL of a chloroform solution with 1 mg/mL of MEHQ were addedto the colorless liquid obtained through refining with a silica gelcolumn (a development solvent satisfied n-hexane:ethyl acetate=3:1), andthe resultant was dried under a low pressure at a temperature of 40degrees Celsius for three hours. Thus, a target compound (1B) wasobtained as a colorless liquid. The yield amount was 1.96 g (4.51 mmol),and the yield was 78.7%. The compound (1B) was then crystallized whilebeing kept in a dark place (melting point: 61° C.).

Measurement results of 1H-NMR (“AVANCE III HD” available from Bruker)being the compound (1B) are shown below.

¹H-NMR (500 MHz, DMSO-d6): δ1.86 (3H, s), 1.87 (3H, s), 4.39-4.43 (1H,dd), 4.49-4.52 (2H, dt), 4.59-4.62 (1H, dd), 5.48-5.52 (1H, m), 5.70(2H, t), 6.04 (2H, s), 7.30-7.46 (5H, m), 7.64-7.66 (2H, d), 7.75-7.77(2H, d), 7.93-7.95 (2H, d)

Example 3 (Synthesis of Compound (1C))

(Synthesis of Intermediate Compound (c1))

5.00 g (20.4 mmol) of 4-bromoisophthalic acid, 10.63 g (102.1 mmol) of2,2-dimethyl-1,3-propanediol, and 150 mL of tetrahydrofuran(dehydration) were measured and put in a reactor vessel, and theresultant was stirred to obtain a uniform solution. 9.39 g (49.0 mmol)of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride and 249mg (2.04 mmol) of 4-dimethylaminopyridine were added to the resultantand it became a suspension. Stirring was performed at a room temperaturefor one night. After that, when the reaction solution was checked withTLC, it was found that 4-bromoisophthalic acid disappeared. The reactionsolution was concentrated under a low pressure at a temperature of 40degrees Celsius, and then 100 mL of ethyl acetate were added. Theresultant was replaced in a separating funnel, and was washed twice with100 mL of a saturated saline solution. The resultant was replaced inanother vessel, and anhydrous magnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The slightly yellow-colored liquid obtained through refiningwith a silica gel column (a development solvent satisfied n-hexane:ethylacetate=1:1) was dried under a low pressure at a temperature of 70degrees Celsius for three hours. Thus, an intermediate compound (c1) wasobtained. The yield amount was 4.66 g (11.2 mmol), and the yield was54.8%.

(Synthesis of Intermediate Compound (c2))

4.66 g (11.2 mmol) of the intermediate compound (c1), 3.34 g (14.5 mmol)of trans-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene, and 50mL of dioxane were measured and put in a reactor vessel, and theresultant was stirred to obtain a uniform solution. A dilute solution of4.62 g (43.6 mmol) of sodium hydrogen carbonate with 25 ml of pure waterand 258 mg (0.223 mmol) of a tetrakis(triphenylphosphine)palladium(0)complex were added to the resultant. While water at a temperature of 5degrees Celsius was caused to flow through a cooling tube, the resultantwas stirred at a temperature of 110 degrees Celsius for four hours.After that, when the reaction solution was checked with TLC, it wasfound that the intermediate compound (c1) disappeared. At this point, 35mL of a 2N ammonium chloride aqueous solution and 15 mL of2-methyltetrahydrofuran were added to the reaction solution. Theresultant was separated into an organic layer and a water layer by aseparating funnel, and then the water layer was extracted twice by 15 mLof 2-methyltetrahydrofuran. The organic layer and the extracted layerwere collectively washed twice with 50 mL of a saturated salinesolution. The resultant was replaced in another vessel, and anhydrousmagnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The yellow-colored liquid obtained through refining with asilica gel column (a development solvent satisfied n-hexane:ethylacetate=1:1) was dried under a low pressure at a temperature of 70degrees Celsius for three hours. Thus, an intermediate compound (c2) wasobtained. The yield amount was 4.50 g (10.2 mmol), and the yield was91.5%.

(Synthesis of Target Compound (1C))

4.50 g (10.2 mmol) of the intermediate compound (c2), 3.62 g (35.8 mmol)of triethylamine (Et₃N), 90 mg (0.73 mmol) of 4-methoxyphenol (MEHQ),and 50 mL of tetrahydrofuran (dehydration) were measured and put in areactor vessel, and the resultant was stirred to obtain a uniformsolution. After that, the resultant was cooled to a temperature of 0degrees Celsius. 3.20 g (30.6 mmol) of methacryloyl chloride were slowlydropped to the resultant. Stirring was sequentially performed for twohours. After that, when the reaction solution was checked with TLC, itwas found that the intermediate compound (c2) disappeared. At thispoint, 50 mL of a 2N sodium hydroxide aqueous solution were added to thereaction solution. The resultant was separated into an organic layer anda water layer by a separating funnel, and then the water layer wasextracted twice by 10 mL of ethyl acetate. The organic layer and theextracted layer were collectively washed twice with 50 mL of a saturatedsaline solution. The resultant was replaced in another vessel, andanhydrous magnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 40 degreesCelsius. 1 mL of a chloroform solution with 1 mg/mL of MEHQ were addedto the slightly yellow-colored liquid obtained through refining with asilica gel column (a development solvent satisfied n-hexane:ethylacetate=3:1), and the resultant was dried under a low pressure at atemperature of 40 degrees Celsius for three hours. Thus, a targetcompound (1C) was obtained as a light yellow-colored liquid. The yieldamount was 2.53 g (4.39 mmol), and the yield was 42.9%.

Measurement results of 1H-NMR (“AVANCE III HD” available from Bruker)being the compound (1C) are shown below.

1H-NMR (500 MHz, DMSO-d6): δ1.03 (6H, s), 1.05 (6H, s), 1.85 (3H, s),1.87 (3H, s), 3.99 (2H, s), 4.02 (2H, s), 4.15 (2H, s), 4.18 (2H, s),5.64 (1H, t), 5.66 (1H, t), 6.03 (1H, s), 6.05 (1H, s), 7.32-7.42 (4H,m), 7.59-7.60 (2H, d), 7.89-7.92 (1H, d), 8.03-8.04 (1H, d), 8.13-8.15(1H, dd), 8.45 (1H, d)

Example 4 (Synthesis of Compound (1D))

(Synthesis of Intermediate Compound (d1))

5.00 g (20.4 mmol) of 4-bromophthalic acid, 10.63 g (102.1 mmol) of2,2-dimethyl-1,3-propanediol, and 150 mL of tetrahydrofuran(dehydration) were measured and put in a reactor vessel, and theresultant was stirred to obtain a uniform solution. 9.39 g (49.0 mmol)of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride and 249mg (2.04 mmol) of 4-dimethylaminopyridine were added to the resultantand it became a suspension. Stirring was performed at a room temperaturefor three days. After that, when the reaction solution was checked withTLC, it was found that 4-bromophthalic acid disappeared. The reactionsolution was concentrated under a low pressure at a temperature of 40degrees Celsius, and then 100 mL of ethyl acetate were added. Theresultant was replaced in a separating funnel, and was washed twice with100 mL of a saturated saline solution. The resultant was replaced inanother vessel, and anhydrous magnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The colorless liquid obtained through refining with a silicagel column (a development solvent satisfied n-hexane:ethyl acetate=1:1)was dried under a low pressure at a temperature of 70 degrees Celsiusfor three hours. Thus, an intermediate compound (d1) was obtained. Theyield amount was 2.17 g (5.20 mmol), and the yield was 25.5%.

(Synthesis of Intermediate Compound (d2))

2.17 g (5.20 mmol) of the intermediate compound (d1), 1.55 g (6.74 mmol)of trans-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene, and 30mL of dioxane were measured and put in a reactor vessel, and theresultant was stirred to obtain a uniform solution. A dilute solution of2.15 g (20.3 mmol) of sodium hydrogen carbonate with 15 ml of pure waterand 120 mg (0.104 mmol) of a tetrakis(triphenylphosphine)palladium(0)complex were added to the resultant. While water at a temperature of 5degrees Celsius was caused to flow through a cooling tube, the resultantwas stirred at a temperature of 110 degrees Celsius for four hours.After that, when the reaction solution was checked with TLC, it wasfound that the intermediate compound (d1) disappeared. At this point, 20mL of a 2N ammonium chloride aqueous solution and 10 mL of2-methyltetrahydrofuran were added to the reaction solution. Theresultant was separated into an organic layer and a water layer by aseparating funnel, and then the water layer was extracted twice by 10 mLof 2-methyltetrahydrofuran. The organic layer and the extracted layerwere collectively washed twice with 30 mL of a saturated salinesolution. The resultant was replaced in another vessel, and anhydrousmagnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 50 degreesCelsius. The light yellow-colored liquid obtained through refining witha silica gel column (a development solvent satisfied n-hexane:ethylacetate=1:1) was dried under a low pressure at a temperature of 70degrees Celsius for three hours. Thus, an intermediate compound (d2) wasobtained. The yield amount was 1.98 g (4.49 mmol), and the yield was86.4%.

(Synthesis of Target Compound (1D))

1.98 g (4.49 mmol) of the intermediate compound (d2), 1.59 g (15.7 mmol)of triethylamine (Et₃N), 40 mg (0.32 mmol) of 4-methoxyphenol (MEHQ),and 20 mL of tetrahydrofuran (dehydration) were measured and put in areactor vessel, and the resultant was stirred to obtain a uniformsolution. After that, the resultant was cooled to a temperature of 0degrees Celsius. 1.41 g (13.5 mmol) of methacryloyl chloride were slowlydropped to the resultant. Stirring was sequentially performed for twohours. After that, when the reaction solution was checked with TLC, itwas found that the intermediate compound (d2) disappeared. At thispoint, 20 mL of a 2N sodium hydroxide aqueous solution were added to thereaction solution. The resultant was separated into an organic layer anda water layer by a separating funnel, and then the water layer wasextracted twice by 10 mL of ethyl acetate. The organic layer and theextracted layer were collectively washed twice with 30 mL of a saturatedsaline solution. The resultant was replaced in another vessel, andanhydrous magnesium sulfate was added.

Solid matters were removed through filtration, and the filtrate wasconcentrated under a low pressure at a temperature of 40 degreesCelsius. 0.5 mL of a chloroform solution with 1 mg/mL of MEHQ were addedto the colorless liquid obtained through refining with a silica gelcolumn (a development solvent satisfied n-hexane:ethyl acetate=3:1), andthe resultant was dried under a low pressure at a temperature of 40degrees Celsius for three hours. Thus, a target compound (1D) wasobtained as a colorless liquid. The yield amount was 1.57 g (2.72 mmol),and the yield was 60.6%.

Measurement results of 1H-NMR (“AVANCE III HD” available from Bruker)being the compound (1D) are shown below.

¹H-NMR (500 MHz, DMSO-d6): δ1.00 (12H, s), 1.88 (6H, s), 3.95 (2H, s),3.96 (2H, s), 4.08 (2H, s), 4.09 (2H, s), 5.65-5.67 (2H, m), 6.05 (2H,s), 7.31-7.50 (5H, m), 7.66-7.68 (2H, d), 7.80-7.81 (1H, d), 7.88-7.90(2H, m)

<Physical Property Evaluation of Compound> (Measurement and Evaluation)

A refractive index of a compound was measured by using amulti-wavelength refractometer (manufactured by Anton Paar Japan).Refractive indexes n_(C), n_(d), n_(F), and n_(g) were measuredrespectively for a C-line (having a wavelength of 656.3 nm), a d-line(having a wavelength of 587.6 nm), an F-line (having a wavelength of486.1 nm), and a g-line (having a wavelength of 435.8 nm). Further, aθ_(g,F) value and a ν_(d) value were calculated from the expressionsgiven below.

θ_(g,F)=(n _(g) −n _(F))/(n _(F) −n _(C))

ν_(d)(n _(d)−1)(n _(F) −n _(C))

Note that, among the acquired compounds, the crystallized compound (1A)and the crystallized compound (1B) were heated to be melted into aliquid state, and then cooled to a measurement temperature, and arefractive index was measured in a supersaturated liquid state. Thecompound (1C) and the compound (1D) were obtained as a liquid compound,and thus a refractive index was measured in a liquid state as it is at aroom temperature. Results are shown in Table 1.

TABLE 1 EXAMPLE 1 EXAMPLE 2 EXAMPLE 3 EXAMPLE 4 (COMPOUND(1A))(COMPOUND(1B)) (COMPOUND(1C)) (COMPOUND(1D)) n_(c) 1.5868 1.5840 1.55511.5499 n_(d) 1.5971 1.5945 1.5636 1.5577 n_(F) 1.6270 1.6231 1.58781.5798 n_(g) 1.6582 1.6538 1.6139 1.6026 θ_(g, F) 0.776 0.785 0.7980.763 ν_(d) 14.9 15.2 17.2 18.7

II. Production of Resin Precursor and Physical Property EvaluationExamples 5 to 10

The compound (1A), the compound (1B), the compound (1C) and othercomponent were mixed at a ratio shown in Tables 2 to 4, and resinprecursors (1A-1) to (1A-3), a resin precursor (1B-1), a resin precursor(1B-2) and a resin precursor (1C-1) were produced. Then, a state underan ordinary temperature and pressure was confirmed for each of theobtained resin precursors. Note that a ratio of combination in thetables are based on mass % unless otherwise specified.

A component used for each of the resin precursors is indicated.

Main Agent 1 9,9-bis[4- (2-acryloyloxyethoxy)phenyl]fluorene (Formula(i))

Main Agent 2 1,6-diacryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane (Formula(ii))

Compatibility Accelerator: methoxytrypropyleneglycolacrylate (Formula(iii))

Photopolymerization Initiator 1: 1-hydroxy-cyclohexyl-phenyl-ketone(Formula (iv))

Photopolymerization Initiator 2:bis(2-4-6-trimethylbenzoyl)-phenylphosphineoxide (Formula (v))

Radical Scavenger: bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate(Formula (vi))+methyl 1,2,2,6,6-pentamethyl-4-piperidylsebacate (Formula(vii))

Ultraviolet Light Absorber:2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole (Formula (viii))

<Physical Property Evaluation of Resin Precursor> (Production of Samplefor Refractive Index Measurement)

A physical property of each resin precursor was measured in a liquidstate without curing.

(Measurement and Evaluation)

Similarly to the method of measuring a physical property of thecompound, refractive indexes n_(C), n_(d), n_(F), and n_(g) weremeasured for each resin precursor, and a θ_(g,F) value and a ν_(d) valuewere calculated. Results are shown in Tables 2 to 4.

TABLE 2 EXAM- EXAM- EXAM- PLE 5 PLE 6 PLE 7 RESIN PRECURSOR NAME 1A-11A-2 1A-3 COMPOUND (1A) 33.34 25 20 MAIN AGENT 1 25.34 28.5 30.4(COMPOUND (i)) MAIN AGENT 2 34.53 38.85 41.44 (COMPOUND (ii))COMPATIBILITY 2.67 3 3.2 ACCELERATOR (COMPOUND (iii))PHOTOPOLYMERIZATION 1.33 1.5 1.6 INITIATOR 1 (COMPOUND (iv))PHOTOPOLYMERIZATION 0.13 0.15 0.16 INITIATOR 2 (COMPOUND (vi)) RADICALSCAVENGER 1.33 1.5 1.6 (COMPOUND (vi) + (vii)) ULTRAVIOLET LIGHT 1.331.5 1.6 ABSORBER (COMPOUND (viii)) TOTAL(MASS %) 100 100 100 STATE UNDERLIQUID LIQUID LIQUID ORDINARY TEMPERATURE STATE STATE STATE AND PRESSUREn_(C) 1.5314 1.5229 1.5173 n_(d) 1.5378 1.5464 1.5236 n_(F) 1.55731.5292 1.5393 n_(g) 1.5761 1.5229 1.5546 θ_(g, F) 0.726 0.715 0.700ν_(d) 20.8 22.5 23.8

TABLE 3 EXAMPLE 8 EXAMPLE 9 RESIN PRECURSOR NAME 1B-1 1B-2 COMPOUND (1B)50 33.34 MAIN AGENT 1 19 25.34 (COMPOUND (i)) MAIN AGENT 2 25.9 34.53(COMPOUND (ii)) COMPATIBILITY 2 2.67 ACCELERATOR (COMPOUND (iii))PHOTOPOLYMERIZATION 1 1.33 INITIATOR 1 (COMPOUND (iv))PHOTOPOLYMERIZATION 0.1 0.13 INITIATOR 2 (COMPOUND (vi)) RADICALSCAVENGER 1 1.33 (COMPOUND (vi) + (vii)) ULTRAVIOLET LIGHT 1 1.33ABSORBER (COMPOUND (viii)) TOTAL(MASS %) 100 100 STATE UNDER ORDINARYLIQUID LIQUID TEMPERATURE AND STATE STATE PRESSURE n_(C) 1.5423 1.5275n_(d) 1.5493 1.5339 n_(F) 1.5709 1.5518 n_(g) 1.5925 1.5700 θ_(g, F)0.755 0.749 ν_(d) 19.2 22.0

TABLE 4 EXAMPLE 10 RESIN PRECURSOR NAME 1C-1 COMPOUND (1C) 33.34 MAINAGENT 1 25.34 (COMPOUND (i)) MAIN AGENT 2 34.53 (COMPOUND (ii))COMPATIBILITY 2.67 ACCELERATOR (COMPOUND (iii)) PHOTOPOLYMERIZATION 1.33INITIATOR 1 (COMPOUND (iv)) PHOTOPOLYMERIZATION 0.13 INITIATOR 2(COMPOUND (vi)) RADICAL SCAVENGER 1.33 (COMPOUND (vi) + (vii))ULTRAVIOLET LIGHT 1.33 ABSORBER (COMPOUND (viii)) TOTAL(MASS %) 100STATE UNDER ORDINARY LIQUID TEMPERATURE AND STATE PRESSURE n_(C) 1.5173n_(d) 1.5228 n_(F) 1.5393 n_(g) 1.5553 θ_(g, F) 0.727 ν_(d) 23.8

III. Production of Cured Object and Physical Property EvaluationExamples 11 to 16

Each of the resin precursors (1A-1) to (1A-3), the resin precursor(1B-1), the resin precursor (1B-2) and the resin precursor (1C-1) wassandwiched between synthetic quarts (t=1 mm), was irradiated with lightfrom a high luminance mercury xenon lamp (“LC8” manufactured byHamamatsu Photonics) through a filter cutting a wavelength under 385 nmto be cured. With this, cured objects (1A-1) to (1A-3), a cured object(1B-1), a cured object (1B-2) and a cured object (1C-1) were obtained. Astate under an ordinary temperature and pressure was confirmed for eachcured object.

<Physical Property Evaluation of Cured Object> (Production of Sample forRefractive Index Measurement)

A silicone rubber sheet having a rectangular opening was placed on aquartz glass substrate, and the opening was filled with a resinprecursor and then closed with a quartz glass substrate. Subsequently,the resin precursor was irradiated with ultraviolet light through thequartz glass substrate to be cured. Further, the cured object wasreleased, and a sample for refractive index measurement, which had ashape of 15 mm×15 mm and a thickness of 0.5 mm, was obtained.

(Measurement and Evaluation)

Similarly to the method of measuring a physical property of thecompound, refractive indexes n_(C), n_(d), n_(F), and n_(g) weremeasured, and a θ_(g,F) value and an abbe number N_(d) value) werecalculated. Results are shown in Table 5 and Table 6.

TABLE 5 EXAMPLE 11 EXAMPLE 12 EXAMPLE 13 USED RESIN 1A-1 1A-2 1A-3PRECURSOR NAME CURED OBJECT 1A-1 1A-2 1A-3 NAME n_(C) 1.5551 1.54611.5408 n_(d) 1.5621 1.5531 1.5470 n_(F) 1.5805 1.5693 1.5626 n_(g)1.5990 1.5859 1.5777 θ_(g, F) 0.728 0.716 0.693 ν_(d) 22.1 23.8 25.1

TABLE 6 EXAMPLE 14 EXAMPLE 15 EXAMPLE 16 USED RESIN 1B-1 1B-2 1C-1PRECURSOR NAME CURED OBJECT 1B-1 1B-2 1C-1 NAME n_(C) 1.5706 1.55441.5423 n_(d) 1.5783 1.5606 1.5479 n_(F) 1.5993 1.5787 1.5641 n_(g)1.6209 1.5968 1.5798 θ_(g, F) 0.753 0.745 0.720 ν_(d) 20.1 23.1 25.1

It was confirmed from above that the compound and the cured objectobtained from the resin precursor containing the compound in eachexample had a high θ_(g,F) value and a low dispersion characteristic ofa refractive index (ν_(d) value).

Examples 17 to 22

Further, for each cured object shown in Table 5 and Table 6, an innertransmittance 27 days after curing and a wavelength at which the innertransmittance was 80% were measured.

(Production of Sample for Transmittance Measurement)

Similarly to the method of producing a sample for refractive indexmeasurement, which is described above, a sample having a thickness of0.5 mm and a sample having a thickness of 1.0 mm were produced assamples for transmittance measurement for each cured object. Further,the resin precursors that were left to stand for 27 days after curingwere used for measurement.

(Evaluation of Inner Transmittance)

A transmittance was measured for the sample having a thickness of 0.5 mmand the sample having a thickness of 1.0 mm, and converted to an innertransmittance for a thickness of 0.5 mm using the expression givenbelow. For measurement, a spectrophotometer (“UV-4700” manufactured byShimadzu Corporation) was used.

Inner transmittance (%)=(A/B)_([100/(a−b)])×100

A: Transmittance with a thickness of 1.0 mm

B: Transmittance with a thickness of 0.5 mm

a: Actually measured dimension of a sample having a plate thickness of1.0 mm

b: Actually measured dimension of a sample having a plate thickness of0.5 mm

(Wavelength (λ₈₀) at which Inner Transmittance was 80%)

An inner transmittance was measured in a wavelength range from 200 to700 nm, and a wavelength at which an inner transmittance was 80% wasmeasured as λ₈₀.

Results indicating an inner transmittance (%) at each wavelength and awavelength (λ₈₀; unit nm) at which an inner transmittance was 80% inExamples 17 to 22 are shown in Table 7 and Table 8. FIG. 6 is a graphillustrating the inner transmittance (%).

TABLE 7 EXAMPLE 17 EXAMPLE 18 EXAMPLE 19 CURED OBJECT 1A-1 1A-2 1A-3NAME 420 nm 98%  99% 98% 440 nm 99% 100% 99% 460 nm 99% 100% 99% 480 nm99% 100% 99% 500 nm 99% 100% 99% 550 nm 100%  100% 99% 600 nm 100%  100%99% 650 nm 100%  100% 99% λ₈₀ 403 nm 403 nm 404 nm

TABLE 8 EXAMPLE 20 EXAMPLE 21 EXAMPLE 22 CURED OBJECT 1B-1 1B-2 1C-1NAME 420 nm  98%  98%  71% 440 nm  99%  99%  98% 460 nm  99%  99% 100%480 nm 100% 100% 100% 500 nm 100% 100% 100% 550 nm 100% 100% 100% 600 nm100% 100% 100% 650 nm 100% 100% 100% λ₈₀ 402 nm 403 nm 423 nm

What is claimed is:
 1. A compound represented by Formula (1) givenbelow.

(In the formula, R¹ represents a hydrogen atom or a methyl group, X1represents a Ci to 9 alkylene group, or a C_(3 to 6) alkylene group inwhich at least one hydrogen is replaced with an acryloxy group or amethacryloxy group, l¹ represents an integer from 0 to 3, Q¹ representsa hydrogen atom or Formula (2) given below

(In the formula, R² represents a hydrogen atom or a methyl group, X²represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylene groupin which at least one hydrogen is replaced with an acryloxy group or amethacryloxy group, l² represents an integer from 0 to 3, and *represents a bonding site), and Q² represents a hydrogen atom or Formula(3) given below

(In the formula, R³ represents a hydrogen atom or a methyl group, X³represents a C_(1 to 9) alkylene group, or a C_(3 to 6) alkylene groupin which at least one hydrogen is replaced with an acryloxy group or amethacryloxy group, l³ represents an integer from 0 to 3, and *represents a bonding site).)
 2. A resin precursor containing thecompound according to claim 1 and a curable composition.
 3. The resinprecursor according to claim 2, wherein the curable composition is aphotocurable composition.
 4. The resin precursor according to claim 2,wherein the curable composition includes one or more compound selectedfrom a group consisting of a fluorine-containing acrylate compound, afluorine-containing methacrylate compound, an acrylate compound having afluorene structure, a methacrylate compound having a fluorene structure,a diacrylate compound, and a dimethacrylate compound.
 5. The resinprecursor according to claim 2, wherein the curable composition includesone or more compound selected from a group consisting of1,6-diacryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane,1,6-dimethacryloyloxy-2,2,3,3,4,4,5,5-octafluorohexane,9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, and 1,6-hexanedioldiacrylate.
 6. The resin precursor according to claim 2, wherein acontent ratio of the compound represented by Formula (1) is 10 to 90mass %.
 7. A cured object obtained by curing the resin precursoraccording to claim
 2. 8. The cured object according to claim 7, whereina θ_(g,F) value is 0.5 or greater.
 9. The cured object according toclaim 7, wherein a refractive index (n_(d)) with respect to a d-line is1.50 or greater and 1.65 or less.
 10. The cured object according toclaim 7, wherein an abbe number (ν_(d)) is 10 or greater and 40 or less.11. The cured object according to claim 7, wherein an innertransmittance is 80% or greater over a wavelength range from 440 nm to500 nm.
 12. The cured object according to claim 7, wherein a wavelength(λ₈₀) at which an inner transmittance is 80% is 430 nm or less.
 13. Anoptical element using the cured object according to claim
 7. 14. Anoptical system comprising the optical element according to claim
 13. 15.An interchangeable camera lens comprising the optical system accordingto claim
 14. 16. An optical device comprising the optical systemaccording to claim
 14. 17. A cemented lens comprising a first lenselement and a second lens element joined with each other throughintermediation of the cured object according to claim
 7. 18. An opticalsystem comprising the cemented lens according to claim
 17. 19. Aninterchangeable camera lens comprising the optical system according toclaim
 18. 20. An optical device comprising the optical system accordingto claim
 18. 21. A method for manufacturing a cemented lens comprising:a contacting step of contacting a first lens element and a second lenselement with each other through intermediation of the resin precursoraccording to claim 2; and a joining step of curing the resin precursorto join the first lens element and the second lens element with eachother.
 22. The method for manufacturing a cemented lens according toclaim 21, wherein, in the joining step, the resin precursor isirradiated with light to be cured.
 23. The method for manufacturing acemented lens according to claim 22, wherein the light radiates to theresin precursor through the first lens element.
 24. The method formanufacturing a cemented lens according to claim 22, wherein the lightradiates to the resin precursor through the second lens element.